Theoretical Investigation of the Rubicordifolin Cascade

The results of a theoretical investigation on the complex cascade reaction leading to the natural product rubicordifolin are reported. These computations analyze the discrete transformations that are required during the conversion of the vinyl naphthoquinone starting material into the natural produc...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 22; pp. 5162 - 5165
Main Authors Lumb, Jean-Philip, Krinsky, Jamin L, Trauner, Dirk
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.11.2010
Amer Chemical Soc
Subjects
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Furans - chemical synthesis
Furans - chemistry
Models, Molecular
Molecular Structure
Naphthols - chemical synthesis
Naphthols - chemistry
Physical Sciences
Plants, Medicinal - chemistry
Pyrones - chemical synthesis
Pyrones - chemistry
Rubia - chemistry
Science & Technology
Stereoisomerism
DENSITY FUNCTIONALS
ACID
SET
QUINONE METHIDES
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Summary:The results of a theoretical investigation on the complex cascade reaction leading to the natural product rubicordifolin are reported. These computations analyze the discrete transformations that are required during the conversion of the vinyl naphthoquinone starting material into the natural product, including two pseudopericyclic cyclizations as well as a diastereoselective, hetero-Diels−Alder reaction.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol102157d